Solid-phase peptide synthesis in the reverse (N → C) direction

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1815-1817

  Thieriet, Nathalie ^a,c   Guibé, François ^b   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITÉ PARIS SUD   (France)

^c CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE;

ARTICLE; BIOCHEMISTRY; METHODOLOGY; SYNTHESIS;

BIOCHEMISTRY; PEPTIDES;

EID: 0034729589     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0058341     Document Type: Article

References (23)

1. Lloyd-Williams, P.; Albericio, F.; Giralt, E. Chemical Approaches to the Synthesis of Peptides and Proteins; CRC Press: Boca Raton, FL, 1997.
2. (a) Letsinger, R. L.; Kornet, M. J. J. Am. Chem. Soc. 1963, 85, 3045.
3. (b) Felix, A. M.; Merrifield, R. B. J. Am. Chem. Soc. 1970, 92, 1385.
4. (c) Matsueda, R.; Maruyama, H.; Kitazawa, E.; Takahagi, H.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1973, 46, 3240.
5. (d) Henkel, B.; Zhang, L.; Bayer, E. Liebigs Ann. Recl. 1997, 2161.
6. (e) Léger, R.; Yen, R.; She, M. W.; Lee, V. J.; Hecker, S. J. Tetrahedron Lett. 1998, 39, 4171.
7. Songster, M. F.; Barany, G. In Methods in Enzymology, Solid-Phase Peptide Synthesis, Vol 289; Fields, G. B., Eds.; Academic Press: Orlando, FL, 1997; pp 126-174.
8. Barlos, K.; Gatos, D.; Schäfer, W. Angew. Chim., Int. Ed. Engl. 1991, 30, 590.
9. Recently we applied this same orthogonal scheme for the SPPS in the "normal" C → N direction, using the allyloxycarbonyl (Alloc) group as a temporary protecting group for the α-amino function. Gómez-Martínez, P.; Dessolin, M.; Guibé, F.; Albericio, F. J. Chim. Soc., Perkin Trans. 1 1999, 2871.
10. Albericio, F.; Kates, S. A. In Solid-Phase Synthesis: A Practical Guide; Kates, S. A., Albericio, F., Eds.; Marcel Dekker: New York, 2000.
11. Blodgett, J. K.; Brammeier, N. M.; Califano, J. C.; Devin, C.; Tolle, J. Presented at the 16th American Peptide Symposium, Minneapolis,MN, June 26-July 1, 1999; Poster 039.
12. For a review, see: Guibé, F. Tetrahedron 1998, 54, 2967.
13. (a) Dessolin, M.; Guillerez, M. G.; Thieriet, N.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1995, 36, 5741.
14. (b) Thieriet, N.; Gómez-Martínez, P.; Guibé F. Tetrahedron Lett. 1999, 40, 2505.
15. (c) Thieriet, N.; Alsina, J.; Giralt, E.; Guibé, F.; Albericio, F. Tetrahedron Lett. 1997, 38, 7275.
16. Hoeg-Jensen, T.; Olsen, C. E.; Holm, A. J. Org. Chem. 1994, 59, 1257.
17. Thieriet, N.; Albericio, F. Manuscript in preparation.
18. Alsina, J.; Yokum, S. S.; Albericio, F.; Barany, G. J. Org. Chem. 1999, 64, 8761.
19. The uronium derivative of HOPyr and its thio analogue have proven efficient in peptide synthesis. (a) Knorr, R.; Trzeciak, A.; Bannwarth, A.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
20. (b) Bailén, M. A.; Chinchilla, R.; Dodsworth, D. J.; Najera, C. J. Org. Chem. 1999, 64, 8761.
21. 2 (9:1) for 30 min.
22. Albericio, F.; Bofill, J. M.; El-Faham, A.; Triolo, S. A.; Kates, S. A. J. Org. Chem. 1998, 63, 9678.
23. Racemization of the Phe residue is expected to be very low due to the structure of 2-Cl-trityl moiety (there is no possibility of oxazolone formation and the steric hindrance retards the abstraction of the α-proton).